EP0183495A1 - Druckempfindliches Klebemittel - Google Patents

Druckempfindliches Klebemittel Download PDF

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Publication number
EP0183495A1
EP0183495A1 EP85308502A EP85308502A EP0183495A1 EP 0183495 A1 EP0183495 A1 EP 0183495A1 EP 85308502 A EP85308502 A EP 85308502A EP 85308502 A EP85308502 A EP 85308502A EP 0183495 A1 EP0183495 A1 EP 0183495A1
Authority
EP
European Patent Office
Prior art keywords
process according
metal
interpolymer
composition
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP85308502A
Other languages
English (en)
French (fr)
Inventor
John Mcmahon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BP Chemicals Ltd
Original Assignee
BP Chemicals Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd
Publication of EP0183495A1 publication Critical patent/EP0183495A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/064—Copolymers with monomers not covered by C09J133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/54—Inorganic substances
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Definitions

  • the present invention relates to pressure sensitive adhesive compositions and a process for producing the same.
  • PSA Pressure sensitive adhesives
  • PSA Pressure sensitive adhesives
  • Such PSA can be used widely with a range of materials on an industrial scale provided that PSA possess a combination of characteristics including good tackiness, adhesion and cohesive strength, and ability to adhere to different types of surfaces. It is also important for the PSA to retain their adhesive strength over a relatively long duration. PSA must be supplied in a form, such-as a solution, which enables the formation of a thin film without adversely affecting its tackiness, peel and shear strength.
  • compositions capable of meeting substantially all these features can be formulated by a suitable choice of interpolymerisable components.
  • the present invention is a PSA composition
  • a PSA composition comprising:
  • the vinyl monomer (a) is the so called 'hard monomer' in the composition and preferably has a glass transition temperature above 50°C. Vinyl acetate is preferred although other monomers such as vinyl chloride, styrene, vinylidene chloride and acrylonitrile or combinations of these may also be used.
  • the acrylate monomer (b) forms the major essential constituent of the interpolymer and is suitably an ester of an alcohol having up to 20 carbon atoms and acrylic acid or methacrylic acid.
  • they are essentially alkyl acrylates preferably having 4-10 carbon atoms in the alkyl group.
  • Specific examples of such acrylates include butyl acrylate, amyl acrylate, hexyl acrylate, heptyl acrylate, octyl acrylate, nonyl acrylate, decyl acrylate and isomers thereof.
  • Functional alkyl acrylates such as hydroxyethyl methacrylate or dimethyl aminoethyl methacrylate may also be used. Mixtures of one or more of these esters may be used as the acrylate monomer (b). Of these, an isomer of octyl acrylate i.e. 2-ethyl hexyl acrylate is most preferred.
  • the amount of the acrylate (b) present in the interpolymer is suitably from 30-96% w/w, preferably from 50-85% w/w of the polymer composition.
  • the alpha, beta-unsaturated monocarboxylic component (c) in the interpolymer is suitably acrylic acid or methacrylic acid, preferably acrylic acid.
  • the unsaturated monocarboxylic acid is present in an amount from 4-10% w/w, suitably from 4-62 w/w, of the polymer composition.
  • Components (a) to (c) in the composition form the tacky interpolymers of the PSA.
  • the interpolymerisation of components (a)-(c) can be achieved by using a conventional initiator e.g. a peroxide, suitably lauroyl peroxide.
  • the interpolymerisation is preferably carried out in a non-aqueous polar or non-polar solvent or mixture of solvents e.g. ethyl acetate, toluene, heptane etc.
  • the interpolymerisation is suitably carried out by charging a reaction vessel at moderately elevated temperatures with the non-aqueous solvent and then adding to the vessel in a stepwise manner over a period the peroxide initiator dissolved in a mixture of the components (a), (b) and (c).
  • the reaction mixture is maintained at the elevated temperature for a further duration until a solution of the interpolymer having the desired viscosity is obtained.
  • the molecular weight of the polymer composition may be regulated by the addition of a small amount (typically 0.01-2% w/w) of a chain transfer agent which is a mercaptan such as t-dodecyl mercaptan and/or a difunctional monomer which contains at least two carbon-carbon double bonds such as divinyl benzene or hexane diol di(meth)acrylate to the reaction mixture during polymerisation.
  • a chain transfer agent which is a mercaptan such as t-dodecyl mercaptan and/or a difunctional monomer which contains at least two carbon-carbon double bonds such as divinyl benzene or hexane diol di(meth)acrylate
  • diol di(meth)acrylates include those of diethylene glycol, triethylene glycol and tetraethylene glycol.
  • the solution of the adhesive interpolymer so formed is then mixed with a chelated metal alkoxide to form the PSA solution.
  • the metal alkoxides serve to enhance the performance of the interpolymer by crosslinking in the adhesive film and the chelating agent improves the storage stability of the interpolymer solution by reducing its tendency to gel.
  • the metal alkoxide used to form the chelate suitably has a formula R n M(OR') m , wherein M is a metal selected from the group consisting of Groups II, III, IV and V of the Periodic Table; R is an alkyl radical having 1 to 8 carbon atoms or an aryl group having 6 to 16 carbon atoms; R' is an alkyl or an aralkyl group e.g. benzyl having 1 to 18 carbon atoms; n is zero or an integer and m is an integer with a value of at least 2 such that the sum of n + m is equal to the valence of the metal M.
  • M is a metal selected from the group consisting of Groups II, III, IV and V of the Periodic Table
  • R is an alkyl radical having 1 to 8 carbon atoms or an aryl group having 6 to 16 carbon atoms
  • R' is an alkyl or an aralkyl group e.g. benzyl having 1 to
  • alkoxides include the ethoxide, isopropoxide or tert-butoxide of at least one metal selected from magnesium, calcium, strontium, barium, zinc, aluminium, germanium, tin, lanthanum, cerium, titanium, zirconium, hafnium, vanadium, riobium, chromium, iron, cobalt and nickel.
  • the alkoxides may also be double metal alkoxides e.g. sodium zirconium isopropoxide, magnesium aluminium ethoxide or alkyl metal alkoxides e.g. diethoxy ethyl aluminium or dimethyl diisopropoxytitanium.
  • the metal alkoxides, double metal alkoxides or alkyl metal alkoxides have to be chelated in order to minimise gelation during storage.
  • chelating agents that may be used are compounds containing electron donating atoms e.g. oxygen or nitrogen and which are capable of forming coordinate bonds with the metal atoms in the alkoxide.
  • Sper!fic examples of such compounds are glycols, alkanolamines, hydroxy acids, ketoesters, dialdehydes and diketones. Of these 2,4-pentanedione and ethylacetylacetone are most preferred. It is preferable to have an excess of the chelating agent in the PSA.
  • a typical cross-linking agent is a mixture of aluminium isobutoxide and aluminium triethylacetoacetate.
  • the amount of chelated metal alkoxide employed is suitably from 0.01 - 5X w/w based on the interpolymer.
  • the PSA composition may optionally contain in addition auxiliary additives capable of promoting the properties desired in the composition.
  • the composition may contain additional stabilizers such as acetylacetone, moisture scavengers or stabilizers such as trimethylorthoformate and adhesion promoters such as an organosilane containing functional groups, e.g. ureidoalkyltriethoxysilane.
  • the PSA compositions of the present invention may be used in various forms. For instance it can be cast as a free film placed between sheets of paper used in transfer operation. It can also be coated onto substrates to provide adhesive coated substrates. Additional solvents may be used to obtain a PSA composition which has a viscosity adequate to achieve formation of thin films by roller or knife coatings.
  • the substrates that may be coated either directly or by release and transfer coating include tapes, sheets, panels, cellophane, vinyls, cloth, rubber, various laminates and other flexible materials. Rigid materials e.g. badges may also be coated.
  • the dried adhesive compositions forms an adherent tacky layer or film on the coated material and provides a bond of high cohesive strength.
  • Reagent A was charged to a reaction vessel equipped with condenser, agitator and nitrogen purge. This was heated to 76-78°C and the reagent mixture B added over a three hour period while maintaining reactor temperature. Reagent C was charged stepwise over a thirty minute period commencing thirty minutes after the completion of B addition. Reaction temperature was maintained at 76 - 78°C throughout this procedure and for a further two hours to give an interpolymer solution of 56.6% solids with a viscosity of 6600 cPs.
  • composition of the interpolymer formed was as follows:
  • the pressure sensitive adhesive solution formulated as above was then coated onto a release paper and the solvent driven off at 95°C to form a pressure sensitive adhesive film which exhibited a peel strength of 18.5N per 25 mm width when tested between polyester film and aluminium foil.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP85308502A 1984-11-22 1985-11-22 Druckempfindliches Klebemittel Withdrawn EP0183495A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848429519A GB8429519D0 (en) 1984-11-22 1984-11-22 Pressure sensitive adhesives
GB8429519 1984-11-22

Publications (1)

Publication Number Publication Date
EP0183495A1 true EP0183495A1 (de) 1986-06-04

Family

ID=10570102

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85308502A Withdrawn EP0183495A1 (de) 1984-11-22 1985-11-22 Druckempfindliches Klebemittel

Country Status (2)

Country Link
EP (1) EP0183495A1 (de)
GB (1) GB8429519D0 (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5194486A (en) * 1989-06-09 1993-03-16 H & N Chemical Company Adhesive
US5214094A (en) * 1989-06-09 1993-05-25 H. & N. Chemical Company Method of preparing pressure sensitive adhesives having interpolymers with internal crosslinking monomers
KR101247639B1 (ko) * 2009-12-31 2013-03-29 동아대학교 산학협력단 전분 또는 식물 생체 바이오매스로부터 하이드록시메틸푸르푸랄을 생산하는 방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4360638A (en) * 1982-01-13 1982-11-23 Rohm And Haas Company Pressure sensitive hot melt adhesive

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4360638A (en) * 1982-01-13 1982-11-23 Rohm And Haas Company Pressure sensitive hot melt adhesive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 80, 1974, page 32, no. 37871n, Columbus, Ohio, US; & JP - A - 73 14 172 (SONY CORP.) 04-05-1973 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5194486A (en) * 1989-06-09 1993-03-16 H & N Chemical Company Adhesive
US5214094A (en) * 1989-06-09 1993-05-25 H. & N. Chemical Company Method of preparing pressure sensitive adhesives having interpolymers with internal crosslinking monomers
KR101247639B1 (ko) * 2009-12-31 2013-03-29 동아대학교 산학협력단 전분 또는 식물 생체 바이오매스로부터 하이드록시메틸푸르푸랄을 생산하는 방법

Also Published As

Publication number Publication date
GB8429519D0 (en) 1985-01-03

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Inventor name: MCMAHON, JOHN